56733-55-2Relevant academic research and scientific papers
Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks
Bennett, Clay S.,DeYong, Ashley E.,Florek, John,Nguyen, Tu-Anh,Pohl, Nicola L. B.,Stamper, Gavin,Vasquez, Olivea,Yalamanchili, Subbarao,Zsikla, Alexander
, p. 23171 - 23175 (2021/09/25)
An automated continuous flow system capable of producing protected deoxy-sugar donors from commercial material is described. Four 2,6-dideoxy and two 3-amino-2,3,6-trideoxy sugars with orthogonal protecting groups were synthesized in 11–32 % overall yields in 74–131.5 minutes of total reaction time. Several of the reactions were able to be concatenated into a continuous process, avoiding the need for chromatographic purification of intermediates. The modular nature of the experimental setup allowed for reaction streams to be split into different lines for the parallel synthesis of multiple donors. Further, the continuous flow processes were fully automated and described through the design of an open-source Python-controlled automation platform.
Rapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization
Yalamanchili, Subbarao,Miller, William,Chen, Xizhao,Bennett, Clay S.
, p. 9646 - 9651 (2019/12/02)
A flexible de novo route capable of producing libraries of 2,6-dideoxy sugars is described. We have found that Au(JackiePhos)SbF6MeCN promotes the conversion of homopropargyl orthoesters into functionalized 2,3-dihydro-4H-pyran-4-ones in good t
Simple oxidation of 3-O-silylated glycals: Application in deblocking 3-0-protected glycals
Kirschning, Andreas,Hary, Ulrike,Plumeier, Claus,Ries, Monika,Rose, Lars
, p. 519 - 528 (2007/10/03)
A high yielding allylic oxidation of 3-O-siIylated glycals 5-10 with the reagent system PhI(OAc)2-TMSN3 is presented. The iodine(m) species generated under these conditions is a lot more effective for generating carbohydrate-derived 3-trialkylsiloxy-2,3-d
Oxidation of Fully Protected Glycals by Hypervalent Iodine Reagents
Kirschning, Andreas
, p. 1228 - 1232 (2007/10/02)
A new application of organoiodine(III) is presented.Fully protected glycals are directly converted into 2,3-dihydro-4H-pyran-4-ones by benzene (PhI(OH)OTs, 1).The detailed study reveals that this conversion is independent of the rel
